Ask The Compound

Practical tips for sizing a retirement nest egg and tracking progress with simple benchmarks. A lively debate about what counts as middle class versus rich and how mindset and location matter. A clear look at whether under-40s should hold bonds and the trade-offs between cash, T-bills, and longer-term bonds. Advice on saving while using GI Bill and VA benefits and strategies for late-stage catch-up saving.

Nick Maggiulli, data-driven finance writer and author of Of Dollars and Data, joins to debate private markets versus U.S. housing. He explores why private assets might struggle and dives into regional housing risks and demographic effects. They unpack buy-borrow-die mechanics, a 7.25% guaranteed offer dilemma, solvency concerns, and tax and account tradeoffs in short, lively conversations.

Blair duQuesnay, a financial planner and Bell Curve newsletter writer, offers practical planning tips. Barry Ritholtz, founder of Ritholtz Wealth Management, gives macro and market commentary. They discuss why markets shrug off shocks, how geopolitics and oil affect recession odds, where different asset classes might head, and practical advice on career breaks and concentrated-stock risk.

On episode 212 of Ask The Compound, Ben Carlson and Bill Sweet discuss managing risk in an uncertain environment, how much is too much Roth, how the BOXX ETF works, 529 accounts for adults and more. Submit your Ask The Compound questions to ⁠⁠askthecompoundshow@gmail.com⁠⁠  This episode is sponsored by Public. Find out more at https://public.com/ATC 👕 Check out The Compound shop: https://idontshop.com 🎙️Listen to our podcasts: TCAF: https://podcasts.thecompoundnews.com/show/TCAF/ Animal Spirits: https://podcasts.thecompoundnews.com/show/animalspirits/ Ask The Compound: https://podcasts.thecompoundnews.com/show/ATC/ Instagram: https://instagram.com/thecompoundnews Twitter: https://twitter.com/thecompoundnews Tik Tok: https://www.tiktok.com/@thecompoundnews Linkedin: https://www.linkedin.com/company/the-compound-media/ Talk with us about your portfolio or financial plan here: http://ritholtzwealth.com Public Disclosure: Paid endorsement. Brokerage services provided by Open to the Public Investing Inc, member FINRA & SIPC. Investing involves risk. Not investment advice. Generated Assets is an interactive analysis tool by Public Advisors. Output is for informational purposes only and is not an investment recommendation or advice. See disclosures at public.com/disclosures/ga. Past performance does not guarantee future results, and investment values may rise or fall. See terms of match program at https://public.com/disclosures/matchprogram. Matched funds must remain in your account for at least 5 years. Match rate and other terms are subject to change at any time. Investing involves the risk of loss. This podcast is for informational purposes only and should not be or regarded as personalized investment advice or relied upon for investment decisions. Ben Carlson, Josh Brown and Duncan Hill are employees of Ritholtz Wealth Management and may maintain positions in the securities discussed in this video. All opinions expressed by them are solely their own opinion and do not reflect the opinion of Ritholtz Wealth Management. See our disclosures here: https://ritholtzwealth.com/podcast-youtube-disclosures/ The Compound Media, Incorporated, an affiliate of Ritholtz Wealth Management, receives payment from various entities for advertisements in affiliated podcasts, blogs and emails. Inclusion of such advertisements does not constitute or imply endorsement, sponsorship or recommendation thereof, or any affiliation therewith, by the Content Creator or by Ritholtz Wealth Management or any of its employees. For additional advertisement disclaimers see here https://ritholtzwealth.com/advertising-disclaimers #AskTheCompound #Investing #PersonalFinance #Retirement Learn more about your ad choices. Visit megaphone.fm/adchoices

Joe DiCipio, an options market practitioner and author on box spreads, explains how box spread financing works and its risks. Short, clear takes on using box spreads to refinance debt, collateral and margin concerns, and why retail interest has grown. Also covers asset location for taxes, small-business retirement plans, and the idea of coasting on dividends.

Practical rules for when to pay down a mortgage versus investing in stocks. Guidance on whether to pause dollar-cost averaging and how long to hold a house. Currency and tax effects for expats buying US ETFs. Thoughts on home equity liquidity and borrowing options.

Josh Brown, CEO and market commentator at Ritholtz Wealth Management, brings sharp, practical market analysis. He breaks down which software firms are vulnerable to AI and which gain an advantage. He contrasts asset-heavy 'halo' businesses with information-centric SaaS. He also covers trading tactics like trailing stops, plus housing policy and career advice for financial planners.

Bill Sweet, a tax expert and former service member who advises on taxes, retirement, and benefits. They tackle managing a large lump sum versus dollar-cost averaging. They explain new TSP Roth in-plan conversions and when to consider converting. They compare new kids' savings accounts to 529s and discuss health insurance options before Medicare.

They debate whether the 4% withdrawal rule still holds and explore hybrid withdrawal strategies. They dive into diversification, recent asset-class rotations, and the case for rebalancing. They discuss the role of taxable versus tax-advantaged accounts and practical choices around selling or renting a home with a low mortgage rate. Emerging markets and how to invest in them also come up.

Brian Jacobs, a portfolio manager specializing in option-based ETF strategies, shares valuable insights on hedging equity exposure. He explains the mechanics of collars and dynamic puts, enhancing understanding of risk management. The discussion covers buffered ETFs, their growing trend, and how they provide downside protection. Jacobs highlights the importance of tax efficiency for advisors and explores the historical performance of these options. Personal reflections on financial independence and the decision for a spouse to stay home round out this engaging conversation.